Water → methyl 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoate

HRID 1466538노트

반응식

HRID 1466538 반응식
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH3:17][CH:18]([CH3:40])[C@@H:19](OS(C)(=O)=O)[C:20]([NH:22][C@H:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)[CH3:24])=[O:21].O>C1COCC1>[CH3:17][CH:18]([CH3:40])[C@@H:19]([O:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:20]([NH:22][C@H:23]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=1)[CH3:24])=[O:21]

참가 물질

6

반응물 4

HCID 962WaterHCID 31236PhenoxyethanolHCID 23665647Potassium tert-butoxideHCID 86730615methyl 4-[(1S)-1-[[(2R)-3-methyl-2-methylsulfonyloxy-butanoyl]amino]ethyl]benzoate

생성물 1

HCID 86730614methyl 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoate수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Under a nitrogen atmosphere, 2-phenoxyethanol (17.3 mL, 138 mmol) in THF (450 mL) is cooled to 5° C. using an ice water bath and treated dropwise over 5 min with a 1M solution of potassium tert-butoxide in THF (138 mL, 138 mmol). The mixture is stirred for 30 min, and methyl 4-[(1S)-1-[[(2R)-3-methyl-2-methylsulfonyloxy-butanoyl]amino]ethyl]benzoate (45 g, 126 mmol) is added in one portion. The mixture is stirred to room temperature for 1 h, and water (300 mL) is added. The layers are separated, and the aqueous layer is extracted with ethyl acetate (100 mL). The combined organic layers are washed with brine, dried over MgSO4, filtered, and concentrated. The crude material is purified using silica gel column chromatography (750 g cartridge; 20 to 60% ethyl acetate in heptane) to provide the title compound as a white solid (30 g, 60%). MS (m/z): 400.4 (M+1).

후처리

  1. stirringThe mixture is stirred to room temperature for 1 h
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (100 mL)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material is purified

출처 및 근거

ORD 기록
ord-cb875c031a424c439629a95a1017b009
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000043B2

반응 노트

불러오는 중…